Presidential scholars and baseball writers debate who were the greatest. While baseball analysis evolved from qualitative impressions of “experts” to rigorous, data-driven “sabermetrics,” analysis of presidential greatness continues to rely on “old-school” reputational rankings based on surveys of scholars’ qualitative assessments. Presidential-congressional relations and baseball are all about winning, but what fans (of sports and politics) find most intriguing is Wins Above Expectations (WAE)—did the team do better or worse than expected? This paper adapts the Pythagorean Expectations (PE) formula developed to analyze baseball to assess legislative success of presidents from Eisenhower to Obama. A parsimonious regression model and the PE formula predict annual success rates with 90% accuracy. The estimates of WAE from the two approaches, however, are uncorrelated. Regression analysis does not identify any president who systematically exceeded expectations, but sabermetric analysis indicates that Republican presidents outperform Democrats. Neither approach correlates with recent presidential greatness rankings.